My Unattractive Best Friend Is Completely Shallow! How Do I Help Him?


I have around 25 people that I speak/preach  to on Sunday mornings and I stay in contact with through church services or email. Truly, I can foresee that someday any or all of my single students (ranging in age from 22-55) could find the right person, with one exception. Dan is a very overweight (at least 75 pounds), 35 year old male who is quite interested in sports and is somewhat involved in church activities.

What I felt where at least 2 wonderful potential female matches have come along for him to pursue; however, his response is always the same: “I am not attracted to them”, because these females have similar physical characteristics that he has.

Dan is truly one of my best friends and often does activities with my wife and I and our 3 children. His taste in women is so superficial that if an attractive female were to show any interest in him (despite any other similar characteristics) he would leap head over heels for her, and I am afraid would be in deeper trouble.

He sadly does not have the personality it would take to win the type of girl he is dreaming of.   He feels very comfortable around men and ladies that are older and younger. However any girl anywhere near his age or that is the least bit attractive, he cannot even bring himself to speak to her for a lack of confidence. I have advised him that he must compensate for his lack of physical attractiveness with personality, yet he feels that having a nice car or dressing sharply or buying a girl flowers or candy should be all that is required to win the heart of a prospect.   He regularly (4 times per week) will text me to ask if I have found him a woman. I have known  Dan for 20 years and truly don’t know how to help him. His senior pastor has had counseling sessions with him to no avail. Any suggestions?



I know this guy in Los Angeles who is successful in the entertainment business. He doesn’t have the issues that your friend Dan has — no social awkwardness, no obesity – but he is short, heavy and balding. Anyway, a couple of years ago, we were hanging out with friends on a hot July day, and we were watching women go by. I pointed out an attractive brunette passing by on a bicycle.

Just because you’re attracted to a George Clooney or a Angelina Jolie doesn’t mean you have the ability to date them.

“Nah,” he said. “She’s not my type.” I was shocked. I wasn’t aware he was in the position to be so choosy. Oh, but he was. In fact, this man made it very clear that it’s the hardest part of finding a girlfriend was that nobody’s attractive enough for him. He’ll only date women that are “8’s” on a scale of 1-10.

Later that night, we were at a bar. I was chatting up a beautiful woman in her mid 20’s and we spotted my guy friend across the room. “On a scale of 1-10, where would you rank that guy?” I asked her. Without hesitation, she answered:

“He’s a 3.”

If that’s not dating in a nutshell, I don’t know what is.

Despite our iffy self-esteem, we tend to overrate ourselves in terms of what we “deserve” to date. Just because you’re attracted to a George Clooney or a Angelina Jolie doesn’t mean you have the ability to date them….  

After years of witnessing this phenomenon, I actually gave it a name: “The Matchmakers Dilemma”.

Simply put: Most people are 5’s, but they want to date 8’s.

This is why it’s so hard for a Matchmaker to set anyone up.

Because most people don’t think they’re 5’s. Or 3’s. In other words, most people are delusional.

(Sorry to be so crude as to rank people with numbers, but it’s shorthand to describe someone’s physicality and most people can grasp the concept, so…)

In the big bell curve of life, for every 10, there’s a 1; for every 9, there’s a 2; and so on. Most of us are going to fall somewhere in the middle of the bell curve — 4, 5, 6. Most of us are average.

Then why can’t we come to terms with it? Not everyone is of equal attractiveness. Not everyone makes the same living. Not everyone has the same sense of humor. Not everyone is equally personable or kind. Yet we certainly wouldn’t admit that we were below average on any of these things. We’re all Mother Teresa, we all look great for our age, we all love to laugh. Just go on a dating site. You’ll see.

My fiancé quotes an old Friends episode where Joey says that people are allowed to date within 2 slots of themselves. Thus, if you’re a 7, you can date a 6 or an 8. Any more than that, somebody’s slumming.

When I work with clients online, pretty much all of them put the most attractive people on their favorites list. It’s hard to blame them. Why write to “the 4” when you can write to “the 9”? Yet even dozens of rejections later, many still refuse to grasp the fact that they’re overreaching. They feel they deserve a 9.

“I can’t help what I’m attracted to,” they say.

“I can get people like this in real life,” they say.

“I’m not dating anyone short/old//heavy,” they say.

Doesn’t matter if they’re short, old, or heavy. They want what they want.

Dan needs to come to terms with the idea that beautiful women have the option of going out with men who are younger, cuter, thinner, taller, funnier, and more confident than he is. And while it’s no crime to be attracted to a Maxim model, it’s not a very realistic goal for him — or for the majority of American men.

My fiancé quotes an old Friends episode where Joey says that people are allowed to date within 2 slots of themselves. Thus, if you’re a 7, you can date a 6 or an 8. Any more than that, somebody’s slumming.

Any hot woman who dated Dan would be slumming. Which is why he needs to get in touch with what he can command on the open market. It really hurts to say this, but apart from a handful of wealthy men who can attract a hot golddigger, there are few folks who can overcome obesity, lack of personality, and social cluelessness.

If you’re a true friend, Jeff, you should tell Dan the truth. That to get a hot woman, he’s got to slim down. That he should hire a dating coach or study some pick up artists. That setting him up with your church’s finest would be a disaster for all parties involved.

Then again, I’m the guy who wrote “Why You’re Still Single: Things Your Friends Would Tell You If You Promised Not to Get Mad”, so take whatever I say with a grain of salt, would ya?

Let us know how it goes.

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  1. 21

    Another gem of positive contribution from m.

    “Can’t imagine why.”

    And a kudos to Cute Redhead’s post, even if it is a bit off-topic..

    Am I the only one who notices that “Jeff” sells his “shallow” friend down the river to the internet? Great friend. There’s someone you want to share personal details with. *sarcasm* Even if what he says is 100% true, it still is not his business to publish this to the world. “Jeff” needs to drink a pint or 2 of STFU and mind his own business.

    So should we. It would be different if “Jeff’s” friend posted asking for opinions about whether he himself is shallow, thereby putting himself ‘out there.’ However, he did not.

  2. 22

    to Jeff,

    First of all, your 35 year old has to do his own shopping/hunting for a woman.

    Secondly, the type of woman he wants, exists, but, in a much smaller pool of single women.

    Almost seems as if the man is clueless, he can get on the internet join one or several of the PUA clubs. Tell him to hurry, there is lots of reading to be done, and lots and lots of practice approaching women….

  3. 23
    Michael Ejercito

    I was totally with your advice until I got to the part where Dan needs to slim down. I like most of your advice but maybe you need to revisit the statistics on weight loss that even if Dan was one of the lucky few who lost weight there is a 99% chance of him regaining it back within five years. So if he managed to slim down and attract a hottie, in five years if she is as shallow as he is, shell be unhappy in the relationship.
    Why is it so hard to lose weight?

    Do people really have to eat a lot every single day? Are they perpetually hungry?

    Dan has no expectation of women to be the right weight if he is overweight himself.

  4. 24

    Actually, I agree with you. Already the previous thread about PUA made me very uneasy (if only for the fact that it put PUA practices in line with professional relationship councelling).
    If these growing concerns stop me posting comments here, I’ll still be looking in here to read the intelligent posts of you and a few other people.
    By the way, anyone else misses Mrs. Vee?

  5. 25

    This post/question seems appropriate to me.

    Jeff’s friend has asked him for dating help and advice. Jeff has tried to advise his friend, but is unsure of how to proceed given how he feels. So he asks for advice on *his own* problem, which just happens to involve his friend. It happens all the time with husband and wives, best friends, etc. and i don’t think we’d say any of them were selling their partner out when they ask a third part for advice (anonymously i might add)

    Jeff’s friend invited him into his business by asking for help; i didn’t read it as Jeff bulldozing his way in. All in all, the query seems appropriate to me.

  6. 26
    Karl R

    m stated: “I do find it interesting is that peoples’ ‘numbers’ don’t seem to be reflective of their personalities in this discussion. It’s all looks! looks! looks!”

    I think that’s mostly an attempt to stay on topic. In addition, attractiveness is something that most people find important. I’m more strongly biased toward intelligence than appearance, but that’s not a trait that everyone will find as appealing.

    Furthermore, most of Evan’s comments can also be applied to other characteristics. I’ll only date women who are in the top 10% of the population intelligence-wise, and I prefer to date in the top 1%. I’m in the top 1%, so I date my equals or near-equals. The lady I just started dating is in the top 0.1% of the population (or higher). She is “dating down” intelligence-wise by dating me; if she didn’t date down, she’d be dealing with an impossibly small dating pool.

    And if it sounds like I’m a bit of a snob regarding intelligence, you’re right. And I’d be quick to agree that intelligence shouldn’t come ahead of traits like honesty or compassion. You could even make a reasonable arguement that my focus on intelligence is as shallow as Dan’s focus on appearance.

    But for almost everyone (including me), looks will be the one criteria that I’ll be judging by for the first 5 to 10 seconds of encountering someone. Probably because my eyesight is much better than my ESP. We see people before we talk to them (unless I’ve forgotten my glasses).

    m also stated: “But I’m a girl. We think about these things. I guess it really *is* only looks that matter to the guys here.”

    You’re not representative of all women in this society; just like I’m not representative of all men. A little over a year ago I was discussing online dating with a middle-aged woman. She was complaining that all the men who contacted her had pot-bellies, which she found absolutely disgusting. Even the ones who claimed they exercised had pot-bellies.

    As I listened to this woman’s diatribe against men with pot-bellies, I was thinking, “but you have a pot-belly….”

    This woman would not tolerate men who had pot-bellies, even though her own stomach hung over her belt. It’s not just the men who are focused on (and hypocritical about) appearance.

    1. 26.1

      Karl R – thank you for this.   I, too, was thinking recently that my attraction only to very smart men (and frankly my closest friends are in the four sigma group, too) was just as shallow as being attracted only to very beautiful men.   Forgiving myself and continuing to date only the brainiacs, though.

      1. 26.1.1


        ..describe a brainiac….

  7. 27


    please read the original post again. I saw nothing that indicated good old jeff was asked by shallow hal for his help with his shallowness.

    even so, I don’t see where telling the world hal is shallow behind his back is helpful, or marginally the act of a (loyal) friend. jeff should simply tell hal he is on his own, not sell him down the river on the internet.

  8. 28

    Jeff’s friend will either wind up a real life 40 year old virgin, or will have to pay for sex, if he isn’t already. I think what is required here, is not “tough” love, but “brutal, kick you in the ass like you’ve never been kicked in the ass before” love. By rejecting women who are in his league (the 1s and 2s), Dan’s expressing his disapproval with his own “1” or”2″ status, but projecting it onto the women with whom Jeff is trying to arrange a match. It’s like he’s saying, “I’M not fat and undesirable. THEY are.” When he realizes he needs to take the steps necessary to lose the weight, learn some social skills, and feel more confident, he won’t feel the need to reject women who aren’t 9s or 10s in his eyes.

    Jeff can either be the one who kicks him in the ass, or enables his current behavior. It’s up to him.

  9. 29

    Evan, you completely missed the mark here. This is not simply an issue of a 1 wanting a 10 and being self-delusional or shallow.

    I was thinking exactly what Marc just said above — Jeff’s friend was actually rejecting himself when he was rejecting those potential matches “with similar characteristics” (i.e. obese). Also, he rejects others before they can reject him. That’s a person who needs a lot of professional help.

    Jeff should firmly suggest that his friend spend a lot of quality time loving and improving himself before he tries to find a woman. You can’t love someone if you don’t love yourself, and what woman is going to deal with that mess?

    He needs to get on a health program, being at high risk of diabetes, heart disease, and cancer (he may already have 2 out of 3, at age 35). This will take a lifetime of dedication, focus, and strength of mind. Maybe if he can put a little effort into this, he will be able to find something to like about himself.

  10. 30

    @ # 27
    Hi Vino,
    I understand how you come to the conclusion that Dan didn’t ask for Jeff’s help, but once Dan starting texting me 4 times a week asking about whether or not I’d found him a woman, I’d consider that him putting me in his business.

    I just don’t see how Jeff has sold Dan down the river by posting an anonymous question to a third party. He feels how he feels. I’d think after 20 years Jeff would be able to man up and tell Dan how he felt about how he approached dating, and the fact that he can’t isn’t a positive, but to me that’s not the point of the post.
    I guess we’ll just agree to disagree on this one.

  11. 31
    Karl R

    vino, compare the following quotes…

    vino:(#27) “jeff should simply tell hal he is on his own”

    Cathouse Teri:(#1) “Do the world a favor and tell Dan you can’t help him. He’s on his own, regarding women.”

    Steve:(#2) “Nobody can help him … Nobody can push him into these changes. Not even you.”

    Karl R:(#3) “It’s time for Jeff to tell Dan that he’s stopped looking. Put the burden of the search back onto Dan.”

    JuJu:(#11) “I, too, do not think it shouldn’t become his friends problem,”

    Honey:(#12) “I agree with others here that giving him back the reins is the best way to go.”

    It appears that even you agree that Jeff needs to stop trying to help Dan. Unlike the rest of us, however, you’re assuming that Jeff already knew the answer to this question. The rest of us are assuming he didn’t.

    I’m assuming that Jeff’s too close to the problem to see the obvious answer. Not only is Jeff close friend of Dan’s, but he’s also some sort of pastor to Dan. It’s probably not in Jeff’s nature to tell people that he won’t help them.

    The internet is not a private forum for “Jeff” to ask his questions in. It’s better than that. It’s completely anonymous. Anyone could be “Jeff” or “Dan”. For all you know, Cathouse Teri is Jeff and I’m Dan. (Sure, it’s inconsistent with other statements we’ve made, but maybe that’s how she’s protecting our identities.)

  12. 32

    Re. #31
    What I got out of it was Jeff was rather exasperated trying to help Dan for last 20 yrs. He no longer knew what to say, so he wrote to a America’s #1 Dating Expert for advice on what to do. Who better?

    Why this should be construed as embarrassing or “outing” Dan over the internet escapes me. This blog is anonymous and presumably Dan doesn’t read it anyway. Though perhaps he should.

  13. 33

    @Michael Ejercito

    Of course, you’re perfectly right, losing weight is not hard at all, that’s why everyone around you is effortlessly thin, and there’s no such thing as a billion dollar diet industry.

  14. 34

    Greetings Brother Jeff! Have you tried speaking any scripture with Dan, i.e. “Pride goeth before destruction and a haughty spirit before a fall”? Here’s another for him: “An intelligent, competent, and virtuous woman – who is he who can find her? Her value is worth more than gold and far above rubies or pearls.” Proverbs 31:10.

  15. 35

    Another thought (and I apologize if this has been said already): is it possible that Dan is not so much shallow as he has such little self-esteem he’s unconsciously (or maybe consciously) attracted to unattainable women, thereby guaranteeing no risk to himself? If he chose a woman who was closer to “level” or whatever you want to call it, she might reciprocate, and Dan would actually have to put himself out there and be vulnerable. Just a possibility.

  16. 36

    I am one of those people who tried to enlighten a friend who was overweight and not getting what she wanted in her life because of her looks. I persueded her to find an expensive Hollywood stylist and attempt to lose some weight so she could be perceived a more favorable light with men, and in her business. But the whole thing fell apart because I challenged her and told her “what people were saying.” It was horrible! I felt bad, and it kinda began to deteriorate our relationship. I began to realize I was always quietly judging her, and I was wrong, wrong, wrong to get involved! It was none of my business.

  17. 37

    Karl R,

    I am with you on the standards, but how do you measure intelligence? What exactly would constitute being in the 0.1 percentile?

  18. 38

    My point exactly, John. Particularly on the internet.

  19. 39
    Cute Redhead


    I see why you say I was off topic, but in my view not really — I was just approaching the topic from a broader perspective. Granted, I need to fill in the dots.

    The OP’s overweight friend stands accused of being delusional about his prospects with the women he finds acceptable enough to date. Maybe “delusional” is merely an extreme of “not seeing oneself objectively.” I’m not delusional about myself, but I don’t necessarily see myself objectively. And feedback from the world can be confusing. Walk down the street and get comments from strange men. “Wow! I’m hot!” Go on a date with a critical guy who wants a trophy blonde. “Wow, I suck.”

    So these internet dates for me have been the equivalent of posting a tubby pic on a “rate me” site — but with a positive response instead of a negative one. My point: The misperception of our “value” on the dating front can go in either direction.

    Which brings us to the overweight friend’s seeming inflation of his value, which many have interpreted as being low self-esteem in disguise. I would agree with this from my own experience, which is why I asked the question: “Now what?” I had this one idea of myself (not attractive to men in a girly way, a buddy kinda gal) and now I don’t know what I am or how to behave or why these guys like me. It’s very new and uncomfortable! Makes me wanna put on some sweats and a baggy t-shirt and eat 94% fat-free microwave popcorn for dinner. The overweight guy would have to go through some kind of discomfort were he to accept the reality of his situation — that to have a relationship he might have to forge one with a warts-and-all kind of woman — and that the fantasy he has (probably compensatory) will not come to pass.

    That said, like me, he might find that he’s been harder on himself than any prospective partner might be. He might discount a lot going things that he has going for him and that would be a real gift to a partner.

    We all distort reality. That’s why it’s nice to find a loving partner, someone who regards us with honesty and compassion.

  20. 40

    Cute Redhead-
    You say you have gotten more attention from men when you wear a dress, high heels, & make-up. You wonder if you’ve underestimated your looks, you’ve always considered yourself a tomboy. I’d venture it has less to do with your actual looks, as it has to do with a change of attitude you project when you “gussie yourself up”. Perhaps you are more flitatious. Subtly more self-assured. And that is what the men you are meeting are responding to.

    I know my attitude is different when I dress ‘nice’ from when I dress in sweats without makeup. I believe that’s true of alot of women.

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